For decades now, President Vladimir Putin has consistently enjoyed markedly high approval rates and seemingly benefitted from charismatic legitimacy, whereas systemic legal-rational legitimacy has remained on a low level. This article discusses how, through the successful communication of political myth, legitimacy has become ever more personalized in Putin’s Russia, and considers some of the dilemmas inherent in non-democratic settings where legitimacy builds on grounds that are not legal-rational in the Weberian sense.